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Holiday Homes in Ashland

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Ashland holiday homes

A two-story building with large windows and a storefront.

1. TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (62 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is NZ$367
includes taxes & fees
26 Aug - 27 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

2. West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
10.0 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Vijay S.
The price is NZ$663
includes taxes & fees
24 Aug - 25 Aug
West Kill Barnhouse: Ski, Work & Unwind
A large, two-story house with a stone facade, a wooden deck, and a clear sky.

3. Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Windham
The price is NZ$915
includes taxes & fees
2 Sept - 3 Sept
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

4. Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Hensonville
10.0 out of 10, Exceptional, (10 reviews)
"This is a very cute, very clean condo near Windham. Perfect for our family of 4. Would definitely stay again. "
United States
Kimberly K.
The price is NZ$612
includes taxes & fees
24 Aug - 25 Aug
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

5. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (8 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is NZ$889
includes taxes & fees
14 Sept - 15 Sept
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

6. Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills

Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Gilboa
The price is NZ$353
includes taxes & fees
26 Aug - 27 Aug
Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

7. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "
United States
Melissa R.
The price is NZ$938
includes taxes & fees
14 Sept - 15 Sept
2 Min Walk to Windham Town | Hot Tub | Fire Pit
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

8. Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (15 reviews)
"House was very clean and beds were super comfy after a day of skiing ! "
United States
Caroline I.
The price is NZ$741
includes taxes & fees
24 Aug - 25 Aug
Midnight Fox
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

9. Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
The price is NZ$939
includes taxes & fees
24 Aug - 25 Aug
Pines Vignette • Modern 3BR Home in Windham
A blue house with a deck, outdoor seating, and a hot tub.

10. 'The Mountain House:' Windham Retreat w/ Hot Tub!

'The Mountain House:' Windham Retreat w/ Hot Tub!
Windham
10.0 out of 10, Exceptional, (36 reviews)
"Great stay Very comfortable "
United States
Teresa G.
The price is NZ$1,313
includes taxes & fees
27 Aug - 28 Aug
'The Mountain House:' Windham Retreat w/ Hot Tub!
A cozy living room with a wooden ceiling, a sofa, a red chair, a fireplace, and a ceiling fan.

11. Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Hunter
9.8 out of 10, Exceptional, (18 reviews)
"Nice home, spacious, and conveniently located minutes from Hunter. I would stay here again. "
United States
Jim D.
The price is NZ$732
includes taxes & fees
24 Aug - 25 Aug
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
A wooden interior with a central fireplace, benches, and a window offering a forest view.

12. Mountain house with Scandinavian BBQ hut and Hot tub

Mountain house with Scandinavian BBQ hut and Hot tub
Jewett
10.0 out of 10, Exceptional, (73 reviews)
"Beautiful home, comfortable bedding, great amenities, great communication with host, overall lovely property. We loved the jacuzzi, bbq hut & she shed. "
United States
Despina M.
The price is NZ$1,153
includes taxes & fees
24 Aug - 25 Aug
Mountain house with Scandinavian BBQ hut and Hot tub

13. Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street

Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
West Kill
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful setting. Great light throughout the house. Convenient to the ski mountains"
United States
Timothy M.
The price is NZ$938
includes taxes & fees
24 Aug - 25 Aug
Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
A pool area with a 'NO DIVING' sign, wooden benches, and stone walls.

14. Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Windham
10.0 out of 10, Exceptional, (1 review)
"Host had an amazing response time. Very easy to talk with via email. She had very clear and easy instructions on check in and check out. The place had lots of bedding, it was warm and inviting, had everything we needed. My daughter thought the “balcony” on the second floor which over looked the kitchen was cool! "
United States
Soonae S.
The price is NZ$1,113
includes taxes & fees
24 Aug - 25 Aug
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
A playground with a water feature and a green structure.

15. Cozy 2-bedroom house in Haines Falls near Katterskill falls .

Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Haines Falls
10.0 out of 10, Exceptional, (2 reviews)
"Friendly host accommodated all our requests. House is quaint and well-kept and well-stocked for all possible needs."
United States
Simon R.
The price is NZ$614
includes taxes & fees
26 Aug - 27 Aug
Cozy 2-bedroom house in Haines Falls near Katterskill falls .
A cozy log cabin interior with a fireplace, wooden walls, a sofa, a coffee table, and a large window.

16. West Elm Lodge near Skiing • Waterfront • Groups • Breweries

West Elm Lodge near Skiing • Waterfront • Groups • Breweries
West Kill
9.8 out of 10, Exceptional, (11 reviews)
"Great home, great host and we enjoyed our time there. Will plan to stay there again next year!"
United States
dominick s.
The price is NZ$1,228
includes taxes & fees
1 Sept - 2 Sept
West Elm Lodge near Skiing • Waterfront • Groups • Breweries
A modern kitchen with a stainless steel refrigerator, a dining area with a table and chairs, and a living room with a sofa and a lamp.

17. Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.6 out of 10, Exceptional, (17 reviews)
"Everything was perfect!"
United States
Jen C.
The price is NZ$516
includes taxes & fees
24 Aug - 25 Aug
Cozy Waterfall Oasis + Firepit

18. Escape the City. Discover the Heart of the Catskills.

Escape the City. Discover the Heart of the Catskills.
West Kill
10.0 out of 10, Exceptional, (1 review)
"If you've lived in an old house before, then you know what to expect. It was good for our needs during our short stay. The house is spacious and there is lots of light. The beds were comfortable and the water pressure was awesome. There is an a/c in every upstairs bedroom."
United States
Alexandra I.
The price is NZ$1,294
includes taxes & fees
24 Aug - 25 Aug
Escape the City. Discover the Heart of the Catskills.
A wooden dining table with a lamp, a mirror, and a vase with branches.

19. Spacious, stylish barn and Private Creek, Firepit

Spacious, stylish barn and Private Creek, Firepit
Denver
The price is NZ$614
includes taxes & fees
21 Sept - 22 Sept
Spacious, stylish barn and Private Creek, Firepit
A wooden deck with Adirondack chairs, a stone fireplace, and a scenic view.

20. Large Group Catskills Mountain Retreat near Hunter & Windham Mountains

Large Group Catskills Mountain Retreat near Hunter & Windham Mountains
Prattsville
10.0 out of 10, Exceptional, (13 reviews)
"Nice stay to hangout with family!"
United States
rakesh r.
The price is NZ$2,139
includes taxes & fees
22 Sept - 23 Sept
Large Group Catskills Mountain Retreat near Hunter & Windham Mountains
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Hotel Vienna

Hotel Vienna

8/10 Good
"It was good to stay, but some amenities’s quality is not enough for the price. Somehow I liked to stay in this hotel."
Miho 1-night trip
Posted 2 hours ago
Hotel Vienna

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
4,114
Accommodation
553 Holiday Homes
Lowest Price
NZ$164
Highest Price
NZ$540